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As Chris Rock would be the first to tell you, stand-up comedy brilliance doesn't necessarily translate to movie stardom. Onstage, Rock is a virtuoso whose biggest challenge is living up to his own legend; onscreen, he's third banana to Adam Sandler or, at best, a well-liked cartoon zebra. "Richard Pryor has two good movies out of 30 or 40," Rock says. "Rodney Dangerfield had one. So it's easy to look at history and go, 'Maybe I'm not going to get one.' " He pauses. "But I guess you've got to make your own history."

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We look back at the most hilarious, heated and how-did-he-get-away-with-that bits from the comedian and director of 'Top Five'

Rock, who always idolized Woody Allen, is taking one last shot at the writer-director-star thing with December 12th's Top Five, a loose, flashback-laden, oft-uproarious chronicle of a day in the life of a very famous, very bummed-out comedian who's not quite Chris Rock. He directed two previous movies, 2003's Head of State (its improbable premise: a community organizer becomes the first black president), and 2007's unjustly reviled I Think I Love My Wife, but, Rock says, watching Louie and Curb Your Enthusiasm helped inspire him to make a film closer to his life. "This movie is the closest I've gotten to capturing the tone of my stand-up," he says. Rock made Top Five independently, with the support of producer Scott Rudin, and a studio bidding war broke out after an ecstatically received screening at the Toronto Film Festival in September.

Rock arrives alone – no assistant, no publicist – for lunch one early--November afternoon in Manhattan's meatpacking district, pulling out earbuds that had been blasting LCD Soundsystem; he still uses an actual iPod. "Music takes away some of your phone battery," he says. "God forbid someone's trying to kill me and I can't call for help because I was listening to Ja Rule." Rock struggles with normal human interaction a lot less than some of his comedic peers: In conversation, he's instantly warm and engaging, as funny as you'd hope him to be without being manically "on." Still, as he riffs on life, work, politics and the love for hip-hop that suffuses Top Five, he occasionally slips into the faux-aggrieved preacher-man shout of his onstage persona – a sound familiar and loud enough to turn heads at every nearby table.

People seemed freaked by your Saturday Night Live jokes about the Freedom Tower and the Boston Marathon attacks.I work my jokes out the same way they do polls for the president. I go into clubs randomly – nothing to advertise that I'm going to be there – and try out the jokes. If they work, they stay in the act, and if they don't, they don't stay. And those jokes seemed fine. Anyway, it wasn't any edgier than when Sam Kinison did the jokes about Jesus' last words – and I was with him that night, his guest at Saturday Night Live. I was at Catch a Rising Star, joking about crack at this white club on the Upper East Side, with no one laughing except one guy in the back row, who turned out to be Sam. He's like, "Hey, what are you doing tomorrow? I'm hosting Saturday Night Live. You want to come?" I saw him do Jesus' last words – like, he was doing the hammer thing, banging on the stage. I watched him snort coke right before he went on! I was Pat Boone compared to that night.

I hate when guys talks about "I'm edgy." It's not edgy if you're talking about it! Tupac didn't talk about it. He just lived it.

But it's kind of good that you can still freak people out, isn't it?I'm just thinking about making people laugh. I hate when guys talk about "I'm edgy." The worst comics think that way. It's not edgy if you're talking about it! You just live it. Tupac didn't talk about it. He just lived it. It sneaks into your work. Richard Pryor wasn't edgy. Richard Pryor was just Richard Pryor. I'm not Marilyn Manson. I'm not trying to shock people.

Was being writer-director-star a key ambition for you?It's not a key ambition. But who's making those movies? If someone was going to hand me something like Top Five, I'd be more than happy to act in it [laughs]. And, you know, live a life. But if you're a black comic, it's "What version of Beverly Hills Cop can you do?" And by the way, if someone wants to cast me in one of those movies, I'd do those, too. But I've got arty taste, which is great and not great at the same time. I'd rather work with Wes Anderson, but I don't look like Owen Wilson. I'd love to work with Alexander Payne and Richard Link-later. But they don't really do those movies with black people that much. So you gotta make your own. And the black movies of substance tend to be civil rights.

Have you turned down roles in those movies?Yes. Put it this way: I don't want to be in anything that happened before the Jackson 5. Anything before them is just black misery. Everything before the Jackson 5 is essentially slavery, or close to it. So as far as I'm concerned, Michael, Marlon, Tito, Jermaine and Jackie ended slavery.

Chris Rock performs at Laughter Is The Best Medecine II:George Pimentel/Getty

And look how you've repaid them in your stand-up.I know, you'd think I would treat them better!

You grew up being bussed to a white school in Brooklyn, where you were subjected to constant racial bullying. Was it hard to trust white people after that?You know what? Even in all the misery, there was always that Brad Pitt, 12 Years a Slave white person that was nice [laughs]. Yeah. Davey Moskowitz was nice to me. But it's weird. In my family, the older brother was a Five-Percenter, a couple of my younger brothers, for a time – they're not now – were Black Israelites. So there's a cloud of rage around me, but being an artist kind of changes that. No matter what you thought coming in, what ignorant thing you believed, you're in show business for two years, you're like, "OK, I was wrong." It's hard to be mad at any particular group of people when you're an artist.

You seem unlikely to have ever been anything like a Five-Percenter, anyway.Yeah, you just got to be really logical when you're a comedian – to a fault. Like a lawyer's got to believe in the law.

You said that losing your father when you were 23 turned you cold.I don't know if cold is the right word. It's just that when you know people die, it's hard to really get that emotional about anything. Like that scene in Annie Hall, where Woody is at the psychiatrist talking about how the universe is expanding and we're all going to die – so what's the fucking point? And there is something about your dad dying that makes you go, "What's the point? What's the point of any of this shit? What's the point of taking this test in school?"

He didn't get to see your success.He met Eddie Murphy – I guess that's some of my success. Yeah, when your dad dies, you know you're alone. It's just like, your dad is Suge Knight. Suge allows you to act like a fool and make mistakes. But Suge also allows you to make The Chronic! When you got this big bully behind you, you feel like, "I'm gonna try all sorts of shit, I'll do anything." And when you lose your bully, you tend to get a little safer.

It feels like you loosened up on this movie.There was a lot more rehearsal in this movie, a lot more ad-libbing. I totally let people change their dialogue. I'm not like, "You've gotta play it like this!" I'm just welcoming the funk in this one. I'm more George Clinton and less Prince.

Your love for hip-hop is all over it. Did you ever seriously try rapping?Yeah, I did. I got a deal at, like, Atlantic or an Atlantic subsidiary. There's demos of me rapping out there. It was before I was a comedian! [Laughs.] Way before.

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Who'd you sound like?Kind of like [deep voice, slow delivery] "Clap your hands, everybody!" [Laughs.] "I'm Chris Rock, and I want you to know that these are the breaks!" I grew up at a time where somebody gives you a flier, Grandmaster Flash is playing at some armory, some place that's really dangerous if you're not from there. We'd go up and see Flash or Grand Wizard Theodore or Cold Crush Brothers. And, "Oh, Flash scratched last night!" OK, your mother's got a turntable, my mother's got a turntable, let's go down to the Wiz and price mixers.

And when did you give that up?It just fell to the wayside. You get jobs and shit. Honestly, if I had any idea that DJs would make as much as they make now! I still spin sometimes – when I'm in some other country, I'll just get up there.

Someone like Chuck D will say that there needs to be more historical awareness among hip-hop fans, that it's not right that the Stones can play arenas and stadiums and Public Enemy can't.The Stones can play arenas because the Stones have songs that are not purely based on references that you had to be there for. I love Public Enemy. But they don't have "You Can't Always Get What You Want." Kanye will be able to play arenas maybe more than Jay Z honestly, because there's a vulnerability and an emotional thing that happens in his music that doesn't happen in most rap. I love rap, but rap is like comedy: It rots. Comedy rots. Trading Places is a perfect movie, just unbelievably good. But there are other comedies, not nearly as old as Trading Places, that just have references and things in them that aren't funny five years later. And rap's got a lot of that.

Was your only contact with Kanye recording that bit on his album, or do you know him at all?I know him very well.

Is there an element of racism in the way the culture responds to him?To me, this is the way the culture responds to anybody who says they're great. They're not going to respond to him any different than they responded to Muhammad Ali. Ali turned out to be right, but let's not act like people just agreed with him [laughs]. History will tell us if Kanye is right. But I don't know, man. I'm glad he exists. He's the most interesting artist in the history of hip-hop. I can't really fuck with nobody that don't like Kanye.

The story of how you started in stand-up is crazy – you saw listings in the paper for comedy clubs, walked over, went on that night, and killed with jokes you had written on the spot. How was that possible?I had seen Richard Pryor, Eddie Murphy, Bill Cosby and Rodney Dangerfield. My first 15 times onstage I killed – like, really big laughs. Then I got a little cocky, and I proceeded to not get laughs for the next four years. You see it in baseball a lot, where a guy's really good the first month and then basically there's a combination of cockiness and the league adjusting to him.

What kind of jokes were you telling at that early stage?Bunch of dumb shit. Like, "Miles Davis is so black, lightning bugs follow him in the daytime"-dumb shit.

Whoa, mocking Miles Davis.Exactly. Like, who am I? Who the fuck am I?

Was it Eddie who taught you that you needed to study this stuff?As soon as I became a professional, I knew I had to study a little bit. I used to hang out with Colin Quinn – every night, man, for seven years at the same clubs, talking about our sets and comparing ourselves to Richard, George Carlin, Murphy, Cosby. Eddie turned me on to Cosby. As a kid, you might think he's corny. Eddie was like, "No, you cannot take this lightly. This is some of the best shit ever done."

Chris Rock and Eddie MurphySGranitz/WireImage/Getty

Do you think you didn't work hard enough as an SNL cast member?I could've worked harder. And I think I'm dyslexic, slightly – I notice it when I'm reading my kids certain books. I'm like, "Goddamn, this is hard!"

So you're saying a cue-card-driven show was a challenge?[Nods.] What I also learned is that there's only a certain amount of hanging out you can do per your talent, and I hung out a little much for the talent I had.

You mean partying?Partying, girls, drinking, getting high, whatever. Not paying attention. Bought a red Corvette. I'm driving a red Corvette convertible. I have a big-titty-blond girlfriend. That was 1991, it was still gangster to date a white girl. That shit was like, "Who the fuck are you? Rick James?" I dated white girls and had eggs and shit thrown at me – motherfuckers throwing beer cans at me in my convertible. And those were real white girls! These white girls now . . . white men don't even get mad when you're with them 'cause they're not real white girls. Back in '89, '91, you get killed for Loni Anderson. Today, nobody's killing you for fucking Gwyneth Paltrow.

While you were on SNL, you broke out playing the crackhead Pookie in New Jack City, a really serious dramatic role. How did that affect things for you?It's hard to even equate it – like every black person saw me in Jack City. I couldn't move to Manhattan because I couldn't get a fucking cab, and as soon as New Jack City came out, I couldn't take the train either. Michael J. Fox hosted one week, and New Jack was the number-one movie and his was number two. They literally made three movies like that: There's New Jack City, Boyz N the Hood and Menace II Society, and that's pretty much it. And the other two are coming-of-age movies. New Jack's like its own thing – it's a fucking black gangster movie. So it stands alone, in its own genre.

Given that early success, did you imagine more of a two-track career, with more dramatic roles?I had no level of sophistication. I had dropped out of high school. My friends in Brooklyn had regular jobs . . . very blue-collar. I was just going from thing to thing. After New Jack, there was talk of me playing Basquiat, with Julian Schnabel directing. But here's the problem: I didn't know who Schnabel was, and I didn't know who Basquiat was. I could name everybody in the Furious Five, though. There was a little bit of talk about me playing the Chris O'Donnell part in Scent of a Woman, which actually would've been a better movie. Not 'cause of me – it just would've been a better movie with a black kid playing that part. But that's the only time I remember anyone thinking of anything even remotely dramatic around New Jack time.

Was it hard to get culturally black material on SNL back then?It wasn't that it was difficult to get anything black on the show – it was difficult to get anything black on it that didn't deal specifically with race. You know? That's the thing. It's just like how there's not a lot of race stuff in Top Five, but it's as black as any movie you'll see in the next 15 years – it's blacker than The Butler or the Jackie Robinson movie, it's blacker at its core. But it's not about race. It's really black, the way George Clinton's really black, like the Ohio Players – "Fire," "Sweet Sticky Thing" – is just some black shit. That shit is black. Like a white man has nothing to do with this shit.

Post-SNL, you kind of went into the Rocky training camp and made yourself into the kind of stand-up we know, right?Here's what happened: I bought a house, had a mortgage to pay, and I was just like, "Fuck trying to be famous. Let me just pay my bills and immerse myself in stand-up." My goal was to be like George Wallace – or Richard Jeni or Bobby Slayton. Comedians know these guys. They're not household names, but they're amazing comedians. That was my goal. Not to be famous, but to be a working stand-up. Make a great living, get a couple of houses, put the kids through college. It got way bigger, but I just wanted to be one of those guys.

A comedian has to live in his head. All this comedy comes from a lonely place. When you're surrounded by an entourage, you're not living in your head.

And now, it sounds like your big challenge is trying to make your stand-up more personal.As you get older, you got to find topics that aren't reference-dependent. Did you ever watch Bill Cosby Himself? Richard Pryor's Live in Concert is the best stand-up movie ever, but Cosby Himself – sometimes it's even better. There's not one reference in that thing that doesn't play. People deal with emotions in music all the time, but comedians are always talking about what they see. But we seldom talk about what we feel. That's the next thing for me. It's not taking it up a notch, but how do I move forward artistically and not level out? Like we said earlier, what's my "Can't Always Get What You Want"? I just want to figure out more universal, deeper things.

Like the way Louis C.K. digs in?Louie digs in, and I got to dig in a little more.

Louie co-wrote your last movie – did he have advice on this one?"Make it more dramatic." There's a lot of jokes that we shot that we didn't put in 'cause they made the movie too silly. That was the main thing: making sure the drama worked. And it worked – there's more than enough comedy in the movie.

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How closely do you follow politics?I always had, like, a dumb-guy's view of current events. Always kind of know a little bit of what's going on. If I knew any more about current events, I probably wouldn't talk about it. Do I really want to talk about Tim Geithner? No, I'd shoot myself in the head. I had to stop going on the Bill Maher show. Too smart. I'm on, like, the barbershop level. That motherfucker's really talking about politics.

Today's Election Day – are you voting?Here's the weird thing: My dad died on Election Day. The day George Bush Sr. was elected president. Me, my uncle and my brother were leaving the hospital the next day. We'd been up all night, basically trying to keep my father alive, so we didn't know who won. It's like a movie. Literally, on the ground there's a paper with Bush. I'll never forget my uncle was like, "Aw, shit, Bush won too." Like his brother died, and to add insult to injury, Bush won, too. I'm always sad on Election Day, and then Obama gets elected and I'm like, "OK, let me give up this fucking thing of being sad on Election Day – gonna let that go."

Do you have an assessment of Obama at this point in his term?I think he's done well – but it's like, I don't know who Tina Turner's second husband was, but he was better than Ike. Right? Maybe he had faults, maybe he lost his job or whatever, but he was better than Ike.

What could Obama have done differently?As bad as George W. Bush was, he revolutionized the presidency. He was the first president who only served the people that voted for him. He ran the country like a cable network; he only catered to his subscribers. Obama's main fault is not realizing that's kind of what people want. That whole trying-to-make-everybody-happy thing is done. People who voted for him want him to do what Bush did. And whoever's the next president will do what Bush did.

You once said even Nostradamus couldn't see the end of American racism.We're never going to see the end of racism per se. But Obama is like the polio vaccine of racism – people still get polio and die, but there is a vaccine. They don't have to get it. And my kids, you know, it's been 12 years now and there hasn't been one racial incident in my mostly white neighborhood – not even a tiny one.

A good portion of their lives has been spent in the Obama era.And not just Obama. Before him, the secretary of state was black. Even if you're not seeing it intellectually, visually you see these things.

How does having daughters affect the way you think about women's issues?How does it affect the way I think about women? People always want to know what the world would be like if the country was run by women – just ask a black person. We live in a matriarchal society. You'll go to a black church. They'll say bad shit about men all the time. But you never hear, "Women need to step up." No, it's all, "You're the greatest thing that ever walked the Earth."

So women's equality was always a given for you?I'm from Bed-Stuy. In Bed-Stuy, the women do better than the men. My father drove a truck, my mother taught school. My mother had an easier life than my father. Any girl I dated had an easier life than me. They weren't getting picked up by cops and thrown in lineups and shit like that. I don't recall the girls being called nigger or any of that shit. Their stories aren't my stories, and they were in the same school as me. I'm not saying shit doesn't exist. I mean, I think it's shitty that there's no woman talk-show host on late-night TV – how Chelsea Handler does not get one of these jobs is beyond me. But when you're talking to a black man – black women are over you, white women are over you.

To be fair, it doesn't seem like there's a black woman in line for the presidency at the moment.Michelle Obama could be the next president if she wanted to be. You ever seen her speak? She could be married to her husband and denounce him at the same time – she's that good: "My husband was good, but we're going to do things a little differently this time."

The director of the Broadway play you did a few years back said she thought you were sleepwalking through your life. What did you make of that?The play taught me that I could work harder and that there was something to get out of working harder. I remember in school, once you realize you're not going to be an A student, you realize that the A's get treated differently, but B and D are all the same. There is no difference in the treatment of a B student and a D student. Nothing! So there might've been a little bit of that in my career – I'm OK, I'll get work. When I got in the play, I was literally working with the best people in the world, and then with this movie, too, I was just like, "Oh, I can work at this speed. I can be an A student. There's some good shit here in this A club."

How did the actual idea for Top Five come to you?I watch Louie, Seinfeld, Curb Your Enthusiasm. I thought, "Let's do a movie like that, but about the whole idea of black fame." I wanted to make a nuanced black movie. In all black movies, the rich people are always evil. And anybody that's educated is evil, which is honestly the worst stereotype that you can have. Vanessa Williams in Soul Food – you went to college! Oh, my God, she must be horrible. Most Tyler Perry movies, that's what it is. You know, white entertainers do not have a responsibility to a community. Nobody's telling Bradley Cooper to keep it real. Harry Belafonte is mad at Jay Z and Beyoncé, says they don't do enough. But nobody's mad at, uh, who's my man from Maroon 5?

Adam Levine.Yeah, no one's mad at Adam Levine – "What are you doing for people with great haircuts?"

Your character wants to be taken seriously. Is that what you want?I want to be taken seriously for comedy. How's that? America kind of treats comedians as second-class entertainers. Bill Cosby as a writer is every fucking bit as good as Bob Dylan. But no one thinks of him in that way – they just think, "Oh, he's funny." Demetri Martin is probably more of an artist than Rihanna – she's a great singer and entertainer, but Demetri Martin puts that shit on paper. He's writing and creating. It'd be nice if that existed in America. When I'm in, you know, New Zealand, they treat me like I'm Thelonious Monk. Like I'm John Coltrane. When Dave Chappelle is in London, that motherfucker is Miles Davis. That's some shit. You make the money in America, but you are an artist when you leave America.

Two of your biggest heroes – Bill Cosby and Woody Allen – have had heavy allegations made against them. How do you process that?It's hard, man. You separate the work from the thing, and you go, "I really don't know what happened." With Woody, I literally don't know. I mean, I got daughters – I don't want anyone calling my daughter a liar or anything like that. The only thing I can say is, I've never seen anyone accused of anything like that just once.

But does that birthday have significance for you?I mean, the only significance is that my dad died at 55 of natural causes, so I get a little scared that way. It just makes me go, "Oh shit, my mother's going to turn 70." I'm more concerned with my mother's birthday than mine. 'Cause it's them, then us.

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But here you are at 49, and you have this renewed heat around you in movies.What do you do with it? Don't waste it on convertibles.

When you go back on tour, how do you deal with the idea that people are expecting that you live up to everything you've done before?You just got to put in the work. That's all it is. If you watch enough Rocky movies – and there are six of them, three of them are really fucking good – anytime Rocky tried to take a shortcut in training, he got his ass whooped. And, you know, Rocky III, he's in a nice gym and the girls are there kissing his muscles and all that bullshit, and Mr. T beats the shit out of him and then he has to go in the dirty gym with the black guys. There's no shortcut. You got to go in the club and be uncomfortable. You got to go alone. The problem with most comedians, why they get so unusually bad by my age – not bad, but most guys by my age are doing kid movies and they're doing family acts, even the edgiest motherfuckers. I think a lot of it has to do with the entourage. I got nobody. A comedian has to live in his head. You got to be alone. When you're surrounded by people, you're not living in your head. You're just not.

You are surrounded by family, though.Yeah, but that's different – I can go to the comedy club by myself. The average quote-unquote big star has a bodyguard and goes with four people. That's not how you do it. All this comedy comes from a lonely place – you can't hear what's going on in your head if you've always got a lot of people. Especially people who aren't comedians.

Eddie Murphy always talks about going back on the road – do you think he will?I wish he would. Nothing would make me happier, but I don't think he's going back out.

You can't pep-talk him back into that?Everybody's tried. I'm just not even going to have the conversation anymore. Just talk music or boxing.

Who do you like out there?Kevin Hart's new stuff is funny. Hannibal Buress' new stuff is really funny. This is the golden age of stand-up. There hasn't been this many good stand-up comedians since, like, the Fifties. Jim Gaffigan's a monster, he's fucking funny. Ron White is unbelievably funny. Amy Schumer's fucking great, man. A lot of funny people. Aziz Ansari just played the Garden. Bill Burr is hysterical. Louis. The Nineties, that was just a boom of clubs, that was like disco. Artistically, it ain't never been this good.

One of my favorite points you've made is that life isn't short – it's long. Especially if you make the wrong decisions.It's long, dude! People cry when they get five years of jail. Cry! Grown men. Cry. Five years is a long time.

So have you made the right decisions?I think I've fucked up as much as anybody. But I've been lucky enough not to repeat bad decisions – that's the key. Like, let's not make the same mistakes as my other movies. "Hey, what would happen if I worked with a really good producer?" A lot of people when they have stuff that flops – like a movie that gets a 10 on Rotten Tomatoes – they just seek out the people that liked it and listen to nobody else. They put themselves in a world where their failure is not a failure. I never want to be that guy. Life gets long 'cause you keep doing the same shit.